The presently disclosed subject matter discloses a series of novel compounds derived from 5-methyl-2-(prop-1-en-2-yl)cyclohexanol, commonly known as isopulegol, as shown below.
Isopulegol has been used in various consumer products across the flavor and fragrance industry. See U.S. Pat. Nos. 5,773,410 and 6,328,982; U.S. Publication No. 2010/0234260; and Japanese Patent No. JP 6065023.
Specific derivatives of isopulegol, which have incorporated the backbone of 1-methyl-4-isopropenylcyclohexane, are known to possess various sensory attributes. For example, International Patent Publication No. WO 2009/123355 discloses a number of compounds providing a prolonged cooling effect, including various isopulegyl carbonates. International Patent Publication No. WO 2005/023749 discloses various isopulegyl carbonates and methods for producing thereof. International Patent Publication No. WO 2005/115325 discloses both menthyl and isopulegyl polyethers, which provide a cooling effect. German Patent No. DE 2115130 discloses various aliphatic and aromatic isopulegyl esters and uses in fragrance applications thereof. U.S. Patent Publication No. 2012/0165559 discloses compounds having physiological effects, particularly a cooling or warming on the skin or mucous membranes. Additionally, examples of derivatives of 5-methyl-2-isopropyl-cyclohexanol, commonly known as menthol, have been disclosed with varying sensory attributes. See Watson et al., J. Soc. Cosmet. Chem. (1978); 29:185-200; Furrer et al., Chem. Percept. (2008); 1:119-126; U.S. Pat. Nos. 4,150,052; 4,459,425; 6,884,906; and International Patent Publication Nos.: WO 2005/049553; WO 2005/097735; WO 2007/100450; and WO 2010/019730.
It is recognized that combinations of materials (e.g., cooling agent, warming agent, and/or tingling agents) that impart sensory effects to the skin of a subject, such as the oral or nasal cavity or other topical areas, are known in the art. For example, U.S. Pat. No. 6,328,982 discloses cool feeling compositions comprising a cooling ingredient and a warming ingredient, e.g., vanillyl butyl ether. U.S. Pat. Nos. 6,780,443, 6,890,567, and 6,899,901 disclose compositions comprising a warming ingredient, a cooling ingredient, and a tingling ingredient. U.S. Pat. Nos. 6,673,844 and 6,838,106 disclose warming compositions comprising a cooling ingredient and a particular compound.
There remains a substantial interest and a need in the art for new preparations of novel flavor and fragrance components with favorable organoleptic and sensory properties. The presently disclosed subject matter provides a pathway for the development of such compounds derived from isopulegol having desirable sensory properties by inducing various chemical reactions at the hydroxyl functionality.